(3S,6S,7R)-3-(benzyloxymethyl)-7-(hydroxymethyl)-6-hydroxy-4-N-methyl-1,4-diazepan-2-one | 1300637-98-2

• 分子结构分类: 有机化合物
• 英文名称: (3S,6S,7R)-3-(benzyloxymethyl)-7-(hydroxymethyl)-6-hydroxy-4-N-methyl-1,4-diazepan-2-one
• 英文别名: (3S,6S,7R)-6-hydroxy-7-(hydroxymethyl)-4-methyl-3-(phenylmethoxymethyl)-1,4-diazepan-2-one
• CAS: 1300637-98-2
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: XRNHBZPSPPNQDD-RDBSUJKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  82
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,6S,7R)-3-(benzyloxymethyl)-7-(hydroxymethyl)-6-hydroxy-4-N-methyl-1,4-diazepan-2-one 在 氢气 、 钯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (3S,6S,7R)-3,7-dihydroxymethyl-6-hydroxy-4-N-methyl-1,4-diazepan-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a diazepanone-based library of liposidomycins analogs as MraY inhibitors

  摘要：

  New inhibitors of the bacterial tranferase MraY are described. A scaffold strategy based on the diazepanone central core of liposidomycins, natural inhibitors of MraY has been developed. It involves the introduction of key structural fragments required for biological activity on enantiopure diazepanones by reductive amination, esterification and glycosylation. Biological evaluation of these compounds on MraY enzyme revealed interesting inhibitory activity for compounds displaying three fragments on the scaffold: a palmitoyl chain, an aminoribose part and an alkyluracil moiety. The inhibitors were also evaluated on MurG enzyme. The best compounds resulted in inhibition with IC50 values in the 100 mu M range for one or the other enzyme. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.006
• 作为产物：
  描述：

  (3S,6S,7R)-3-((benzyloxy)methyl)-7-((tert-butyldiphenylsilyloxy)methyl)-6-hydroxy-4-methyl-1,4-diazepan-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到(3S,6S,7R)-3-(benzyloxymethyl)-7-(hydroxymethyl)-6-hydroxy-4-N-methyl-1,4-diazepan-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a diazepanone-based library of liposidomycins analogs as MraY inhibitors

  摘要：

  New inhibitors of the bacterial tranferase MraY are described. A scaffold strategy based on the diazepanone central core of liposidomycins, natural inhibitors of MraY has been developed. It involves the introduction of key structural fragments required for biological activity on enantiopure diazepanones by reductive amination, esterification and glycosylation. Biological evaluation of these compounds on MraY enzyme revealed interesting inhibitory activity for compounds displaying three fragments on the scaffold: a palmitoyl chain, an aminoribose part and an alkyluracil moiety. The inhibitors were also evaluated on MurG enzyme. The best compounds resulted in inhibition with IC50 values in the 100 mu M range for one or the other enzyme. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.006